


Ain't It Funny How The Night Moves

by karmascars



Category: Supernatural
Genre: Alternate Version of Season 5, Anal Fingering, Anal Sex, Crack, Established Relationship, First Kiss, First Time, How Is This Dean's Life, Humor, M/M, Masturbation, Mortal Cas, Multiple Orgasms, Not a Date Fic, One-Shot, Oral Sex, PWP, Past Relationship(s), Phone Sex, Prompt Fill, Smut, Surprise Kissing, Surprise Sex, Voyeurism, canon AU, date fic, gratuitous use of the word fuck, sort of
Language: English
Status: Completed
Published: 2015-06-02
Updated: 2015-06-02
Packaged: 2018-04-02 13:00:31
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,578
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4060939
Author URL: https://archiveofourown.org/users/karmascars/pseuds/karmascars
Summary: <blockquote class="userstuff">
              <p>Dean has a plan to ask Cas out, but this particular night does not go as planned. (Everyone's okay with it.)</p>
            </blockquote>





	Ain't It Funny How The Night Moves

**Author's Note:**

  * For [intotheruins](https://archiveofourown.org/users/intotheruins/gifts).



> The prompt was for a fic where Dean tried to ask Cas out on a date, set sometime post- an alternate ending to S5 in which Castiel was not exploded, but fell and became mortal, and Lucifer was defeated/caged in such a way that Sam didn't have to jump. I've been trying to figure out a neat-sounding alternate version of Stull that works, but since this devolved into shameless porn I'm just gonna leave this up here to serve as the explanation. That works, right? 
> 
> Enjoy.
> 
> Title from _Night Moves_ , Bob Seger & the Silver Bullet Band.

_"This doesn't make sense,_ " Sam says, utterly bewildered and muffled by the bathroom door. " _None of these records are adding up. Dean? Are you listening to me? Where did you find this stuff?"_

Dean smirks into the mirror.

"It was, uh, Dad's old phone," he shouts over his left shoulder. "Somebody left a message, said they mailed all that shit to the PO Box. You saw me get it out."

He'd been thorough, wearing gloves and printing mailing labels and then shipping the bulging padded envelope from Virginia a week ago. He even planted a fake voicemail on the old cell phone, though Sam hadn't asked to hear it yet. They pulled through Edwards this morning, and he let Sam tear the mailer open for complete authenticity.

Cas wanted Dean to put more thought into what he did, well. This'll show _him_. He certainly looked interested in the "clippings" (Dean had them copied on newsprint at Kinko's) when Sam pulled them out in the car.

Grimacing at himself in the mirror, Dean shrugs his crimson button-down off his shoulders. It's either this one, or the green. Or no overshirt, because spring has given way to summer and Dean finds himself sweating in just one layer. Cas also said he wants Dean to be himself. Dean looks like different versions of himself in each of these three outfits... which version would Cas like best?

It shouldn't surprise Dean that he's so concerned with what Cas likes or doesn't like or might like or might just disapprove of slightly -- after all, the guy has been his personal guardian angel ever since that whole thing with Zach went belly-up, and he almost just got himself killed for Dean and Dean's little brother. And their surrogate father, which. If Dean sent thank you cards, Bobby would be getting one.

A handle of something. That'll work.

Dean twitches the red shirt all the way off and lets it hit the floor. He reaches for the other. Yeah, this one. Makes his eyes look crazy green, like portals to some alien woods, or like that painting he saw once of a forest with fireflies all around.

He shrugs the shirt on. _Whoa_. It must be the bathroom light... but Dean doesn't know when he last saw the gold flecks in his eyes so clearly.

Cas seems to stare into his eyes a lot. Is he counting those?

Can he still count them, now that -- that he's -- or does he get lost in them like Dean gets lost in Cas' eyes all the time? Talk about _blue_.

Dean studies his face in the mirror, side to side. Does he need to do anything with his hair? Maybe just -- He runs a little water into his fingers, runs his fingers through his hair. Spikes it up a little. He might even pull a runway pout, but that's between him and God.

 _"Dean,"_ Sam yells from outside the door, _"I'm going to the library again. Something just isn't adding up."_

 _Shit!_ "Can you -- uh, can you leave the car?" Dean calls, trying not to sound panicked. He needs the stupid car because the stupid place he's going to take Cas tonight is still twenty miles away. He couldn't go directly there to get their rooms, because that'd look suspicious.

Yes, moreso than zombies that only rise on the twelfth night of a lunar cycle that has a new moon for four nights. (It's something Dean found in a book about Iranian curses)

(Yes, a book about -- shut up. It was stuffed in the couch seam at Bobby's. Smelled like vinegar and barbecue sauce. Dean was hungry the whole time he was reading it.)

 _"Don't you think a hook-up is a little less important than zombies?"_ Sam says with stark disapproval. _"I thought you were trying to turn over a new leaf -- what happened to not sleeping around on the job?"_

"When did I ever -- oh."

 _"Yeah, oh. I'm taking the car. If you want to charm the pants off a certain someone over in 12B, I suggest you pick a place within walking distance."_ Through the door, the car keys jingle ominously.

Cas doesn't want steak and stilted conversation, he wants Maylene's famous deep-dish apple cobbler from the Junction Diner in Kickapoo. Dean doesn't even care that cobbler is basically just the bastard cousin of pie and that making something like that in a rectangle with crumbs for the top is totally cheating. It's the best thing he's ever had in his mouth. Castiel must try it.

It's twenty fucking miles away.

Darting away from the mirror so he doesn't have to see the shameful flush he feels creeping over his face, Dean yanks the bathroom door open. "Damnit, Sammy, I have a plan!"

Sam is standing in the middle of the room, he doesn't even have his shoes on, and the keys are dangling from one finger. He has the biggest shit-eating smirk on his face, and his eyebrows are way high up on his forehead, trying to mate with his hair. (Their babies would be miniature Cousin Its or, oh fuck no, furbies. Dean shudders inwardly.)

"Plan, huh?" Sam squints at him. "Dude, is there _product_ in your hair?"

"No," Dean says. "Shut up."

Sam just gives him a look.

"Shut the fuck up!" Dean barks. "It's water. What are you doing?"

His brother laughs, and tosses him the keys. Dean catches them. "What -- huh?"

The mailer envelope comes faster than he expects it and smacks him right in the chest.

"Way to be subtle, jerk." Sam is laughing at him. "The 'victims' are all the members of Deep Purple and, unless I'm way off mark here, all the main cast members of M*A*S*H."

"Now, wait just a --"

"That horribly jarring mix of Etruscan and Russian that you used for the 'curse' basically translates to gibberish, but I get what you were trying to say and I forgive you." Sam's mouth does some kind of gymnastics trying to stay straight for that one. Dean's about 97% sure that the mess of words said _You are fuck a goat on stilts_. It was the closest he could get.

Dean can't say a single thing in his own defense. He stands there getting redder, and realizes he's holding his breath the exact instant Sam takes pity on him and says, "Does Cas know he's going out tonight?"

There's a lump in his throat right now for some reason, but Dean coughs and works past it. "Nah," he says, trying for casual. "Figured I'd surprise him."

Y'know, Dean really hates that look on Sam's face, the mix of amusement and actual pity and that shimmer there that Dean tries really hard not to think about.

Shaking his head, Sam is moving to the room phone. He picks up the receiver, and dials.

Dean clues in late. "Wait, what are you --"

"Hey, Cas," Sam says softly. His warm little smile widens, gets warmer, and Dean imagines he can hear the deep, rich tones of Castiel's voice answering.

 _"Sam,"_ he hisses.

"Dean wanted to ask you something," Sam says, flicking fingers at him like he's a buzzing fly. "Could he mayb-- h-huh? You're --"

A noise escapes Sam that Dean has never heard before.

His brother whispers, "You're doing what?"

And then Sam is sitting down on the bed, clutching the phone to his ear, and he's sitting so tensely that Dean can see the lines of each muscle under his clothes.

Dean is _intensely_ curious.

He makes his way over to the bed, treading silently, eyes trained on the way Sam's other hand has found its way to his mouth. Dean sinks down beside him just as that hand forms a fist, and Sam bites down.

There is some kind of static-y sound coming out of the tinny speaker. Dean presses his ear to the outside of the handset just in time to identify that sound as a drawn-out groan.

 _"Oh, Sam, it's so hard,"_ Castiel says.

All of Dean's blood is suddenly _elsewhere_.

He nearly doubles over, hard as fucking nails so fast he feels lightheaded. He has no doubt that Sam is in the same predicament -- shit, his brother is frozen, biting down on his finger so hard that the flesh is turning white.

Over the phone, Cas is panting harshly. Dean imagines he can hear the slick slide of a palm over smooth, heated skin.

 _"Are you there, Dean?"_ Cas suddenly asks.

"Yeah," Dean croaks. His heart is pounding. He blinks, and realizes that for some reason his eyes were fixed on the bulge in Sam's pants. Sam sucks in a shuddering breath, Dean knows he saw.

He doesn't know if he cares.

 _"Dean,"_ Castiel whines, _"I have been thinking about telling you that I do this, and it -- ohh, it makes it feel better."_

"Yeah, Cas." Fuck, is that his voice? "You still got your clothes on, baby, or what?"

 _"Yes, I -- yes, Dean, I was getting ready to c-- come and see y--"_ He breaks off in a gasp. _"Oh, Dean, Sam, I'm going to -- oh, oh,"_ his voice climbs higher, louder, and when he shouts out his orgasm Dean can't control the animal noise that slips out of his mouth.

" _Dean_ ," Sam moans, sounding just as embarrassed as he is aroused. He's looking away from Dean, clutching his thigh with a trembling hand.

Dean just sits there and focuses on breathing. Arousal is zinging around inside his body, lighting him up like a pinball machine. He's reeling. _What -- what the fuck was that? What just happened? What's still happening?_

Is this _his_ life?

" _Dean_ , _Sam_ ," Castiel says from the phone, " _I will be there momentarily. I am... not clean._ "

A laugh hisses and spits its way from Dean. He slumps forward, hands sliding down his thighs as his elbows lock, and just shakes his head.

Sam slips the phone back into its cradle. The click is startlingly loud. He rocks the bed when he stands, hands twitching down by his sides. The hard line of his cock is about a foot from Dean's face, distending the front of Sam's jeans.

"I'm --" Sam says. He takes an unsteady breath.

Then he bolts for the bathroom. Shuts the door, and locks it.

Dean stares at the closed door sideways, looking past his arm. There's no water running, no fan switched on, and so he hears with perfect clarity the sound of Sam's zipper getting yanked hurriedly down, the rustle of fabric, and Sam's breath hitching on a barely audible whine when (Dean guesses) he gets himself in hand.

Well, there's no way Dean's not taking advantage of this.

He swings his legs up on the bed, lying back with a clench to his abs as he works his belt open, shimmies his jeans down his thighs a little. He's wearing his loosest pair of boxers, having assumed that he'd get at least half-hard out on a _date_ with _Cas_. Now, his cock is so hard it's aching, flushed red and so full in his hand. He strokes and even that lightest touch has him arching into it. He won't need much, but goddamn, he _needs_.

He can hear Sam, too, and that's not making this any easier to parse. Not with a brain operating on two single blood cells. Dean squeezes himself up the shaft, milking out a dribble of precome, and he smears that around on the head. He hisses when a callused fingertip drags on the sensitive underside. That one spot, there atop the glans, it's fucking _good_  --

Sam moans in the bathroom, deep and throaty, and something slams around with a clank. The toilet tank lid, what is he --

An image flashes through Dean's mind of Sam bent over, fingering himself _deep_ , fisting his cock with quick strokes, his face slack with pleasure.

" _Ungh, fuck,_ " punches out of Dean, his hips buck up, and he comes spectacularly all over the clothes it took him forever to pick out.

He's shaking with it, still practically blind, when Castiel stumbles through the door, his suit mussed and askew. He's missing the trench coat completely.

"Sam, Dean, I need --" he's saying, but he stops still and stares when he sees Dean. " _Oh_."

Dean can only lie there, stunned.

In that silence, the space filled only with their panting breaths, Sam comes. The sounds he makes race up and down Dean's spine.

Dean blinks and Castiel is leaning over him, lithe arms braced on either side of his head, and then Castiel kisses him so fiercely that Dean is driven into the springs of the shitty mattress. As first kisses go, it's a doozy. Dean tilts his head into it, grabs at solid shoulders and back and the nape of Castiel's neck. He bites at Castiel's lips and demands entrance, sucking Castiel's tongue into his own mouth the instant he gets inside. The kiss is too wide, too wet, but Dean loves it, and the only thing he might love more is the way Sam lets out a wild moan when he sees and thunks to his knees on the carpet.

"Jesus _Christ_ , you guys."

In response, Dean rips open the buttons of Castiel's suit jacket and starts shoving it off his shoulders.

Grappling, snatching, with wanton tearing of cloth, they get each other naked roughly. Dean's jeans only make it to his knees, his boxers torn clean off his body in a feat of strength that he wouldn't have thought Castiel capable of anymore. Cas is still wearing his tie, and one pant leg. His shirt is a lost cause. (Dean's is somewhere over by the AC unit.) Castiel's hair is rucked up like he's been sleeping, and his blue eyes are fever-bright, staring down at Dean with the rest of his face in shadow.

"Dean," he says. "I need you."

"How do you want me?" Dean whispers.

Castiel swallows. "Your -- your cock, Dean, I want to -- what was the -- _ride you_ , I want to ride you."

Dean has to tip his head back and briefly close his eyes against the searing heat of that whole stammered sentence. "Jesus, Cas."

"Is -- can I do that?" Castiel's voice is a burnt-dark husk. "Can I ride you, Dean?"

"Do it," Sam says, much closer. Dean's head whips to the side. Sam is there at the side of the bed, still on his knees, and what Dean can see of him is swaying in such a way that tells Dean his brother's hips are working down below the edge of the mattress. "Do it."

"Yeah," Dean says absently, hands roving Castiel's thighs as Cas lifts up and reaches behind himself. His back forms a sinuous arch, his lips part, his eyelids flutter. He's got at least one finger inside himself. Dean bites at his lip, drinking Castiel in.

"Two," Castiel gasps suddenly. "I've got -- I worked up to three earlier, I'm still so slick inside, _Deannn_ ," he whines as he moves. Dean's dick twitches. "But," Cas adds, panting, "you look larger to me."

"Try it, you'll like it," Dean jokes on autopilot. His voice comes out strained. Castiel's cock is bobbing tantalizingly close, and Dean bets he could sit up just enough to suck the tip into his mouth.

He decides to try while Cas is... occupied.

He lurches up, seals his lips around the head. With a shout, Castiel bucks his hips, feeding Dean another inch, jerking between his fingers and Dean's mouth. Dean sucks and licks as best he can. He drags the tip of his tongue around the satin flesh, testing the way each separate sensation makes Castiel react. It's delicious on so many levels. Cas is gorgeous, a wet dream of body and voice, fucking back on his fingers like it's going out of style. But languidly. Liquidly. Something to describe the way it all flows before Dean's eyes when he sits back to just watch, because it's melting Dean's mind as he drinks it in.

From the way Sam's breathing has changed, he's got a hand on himself again. He's flushed in the corner of Dean's eye, staring up at what's probably an even better view of Castiel holding himself open, biting a lip, and sinking down on to Dean.

Dean holds himself steady and stops breathing as tight, hot perfection envelops him. Inch by inch, with moans just this pleasant side of pained, Cas sinks with steady determination until he's seated astride Dean's hips. His ass clenches around Dean rapid-fire, getting used to being full; Castiel flushes and Dean lets out a surprised whine when his cock twitches inside, sealing them even tighter together.

" _Fuck,_ " Sam's panting under his breath, " _f_ _uck, you guys, fuck."_ Castiel leans forward, planting his hands on either side of Dean's head. He smiles, and begins to move.

Dean's eyes roll back in his head.

God, _oh_ , what the fuck is this, his whole body is moaning, screaming as Castiel rides him so slowly and sensually that it seems unreal. Those gorgeous thighs tense, he rises, and Dean draws in a shuddering breath. Cas sinks back down with a groan; Dean, letting his breath out tremulously, gets flooded with pleasure and slides his hands over every inch of Cas that he can reach. He gets to the tie, and wraps it around his hand. Reels Cas in by it, inch by inch, until they're nose to nose.

"Gonna kiss you again," he growls, Castiel's wanting noise lost against his lips when Dean yanks him down by the tie and plasters their mouths together.

Their tongues mimic what their hips are doing, a slow dirty grind, seeking out all the available space and filling it with heat. They writhe together so completely that Dean is starting to forget where he ends and this amazing man begins. He lets the tie slide from his slackened grip when Castiel sits up, using some kind of tremendous thigh control to keep his grinding down on Dean at that same mind-blowing level of intensity. Dean's hips and cock are fused to him. Dean can't even blink.

"Fuck him faster," Sam grinds out from beside him, breaking the spell. "Go on, Dean. Fuck him like you mean it."

Dean's about to say something to him like, _"Can't rush art, Sammy,"_ but then Cas is moaning, "Oh, please, _yes_ ," and Dean can't help but tighten his grip, dig in his heels, and thrust up sharp and quick. Castiel squeals, throws his head back, and takes it. Oh, he takes it. Dean is _pounding_ up into him, hips smacking that pert ass, fingers digging in. Sam is jacking off to it so hard that Dean can hear the slapslide of skin on skin -- he's panting, he sounds close, and suddenly Dean feels bolder than he has in a very long time.

"Sammy," he says breathlessly, turning from one beautiful sight to another, "let me."

There's no word for the sound Sam makes, staring across at Dean, his whole arm trembling with the effort it's taking to grip himself at the base and not come from hearing what Dean just said. Dean doesn't quit fucking Cas, setting a brutal pace, but he holds Sam's gaze and tries to convey through that look alone what he's asking for. What it means to both of them. Sam's eyes speak just as loudly.

They haven't been together that way since. Well. When you don't trust one another, when one after the other of you has been _dead_  -- and then, yknow, Apocalypse. Dean's been busy. They both have.

And he's pretty sure, maybe 67%, that before tonight Sam wouldn't have wanted him. Sam found more of himself during those four months than demon blood, and Dean knows it, and Dean's not an idiot. But it's been so long, and now with everything that's happened, everything that just _ended_  -- well, he's feeling brave.

Looks like it's going to pay off. Sam rises to his feet, the ruddy head of his cock and several inches poking out of his fist. Dean salivates just seeing it again. He loves Sam, sure, he loves his brother's dorky brain and enormous heart and weird quirks more than a lot of things, but he _really_ missed Sam's cock.

Cas is making frantic noises like he can't believe what he's seeing, ass clenching tight around Dean, while Sam draws nearer, slowly, like Dean's gonna run away from something he's _asking for_. He sways close enough just as Dean grunts in dissatisfaction and grabs at him, lunging and sucking what of Sam he can into his mouth. It's an awkward angle but it is _well worth_ the neck cramps to hear that sort of strangled groan coming from Sam again.

Something warm dribbles into the thatch of hair at the base of Dean's cock. He grabs at it, _Castiel's precome_ , and his hand finds Castiel's cock.

"Ah, Dean!"

Dean hums his appreciation around Sam, who echoes him. Sam's whole body is trembling, the _bed_ is trembling. He's fighting not to move. Dean gets an arm between his legs and wraps around his left, hand cupping Sam's ass cheek. Urging him in deeper, until neatly trimmed hair is brushing the tip of his nose. He inhales, swimming in Sam, familiarity rushing over him as his brother begins to move.

Sam finds his rhythm, slow and pushing in deep with each thrust, and then Dean finds a counterrhythm with the rest of his body, fucking up into Castiel, who swivels down harder on him when he finds the rhyhthm, too. Dean's hand works over Castiel's cock. Suddenly they're all three moving together, synchronized in the dirtiest symphony it's ever been Dean's pleasure to witness, let alone be part of. He is tied up between the two people he cares about the most, full and filling, tasting old favorites and satisfying new-found cravings. It's the best night of his life.

His orgasm is a slow, spreading burst, a rush like time-lapse entropy. All of his nerve endings _sigh_.

Then the shakes start, the wave crests. His eyes roll back in his head and he's arching up into Cas, seizing, wracked with absolute pleasure. His mouth goes slack around Sam, but with the way he must look, it doesn't matter. Sam starts fucking his face in earnest, grabbing at him and manhandling him the way he used to. Dean doesn't bother trying to control his whimpers. Especially not when Cas screws down on his cock -- which is still hard, but so fucking sensitive -- angling for his own prostate like Dean is just a toy. It's _hot_.

Two more strikes in that spot and Castiel comes with a shout -- he grabs at Sam and hauls him in for a kiss, which Sam meets with a shocked look and then something out of the movies, running a hand up Castiel's jaw. Sam's hips pump one, two, three times against Dean's face and he's coming too, groaning into Castiel's mouth, Cas lapping the sound up eagerly. Dean swallows as much as he can, a slight trickle running out along the side of his face. He mouths at Sam's cock when he draws off.

They all three tremble together. The kiss above Dean slows, turns to smooches, and then they're both gazing down at Dean with a satisfied glow.

"I --" _taste like spunk_ , he means to say, but they kiss him before he can. It's probably for the best. When he's let up for air, his eyes lazy-lidded and all three pairs of lips tacky with shared fluid, he's changed his mind. He looks at Castiel and says instead, "I wanted to ask you to dinner."

"Oh." Cas blinks down at him. "Do you still want to?"

Dean tilts his head (Sam snorts, because _oh, right, that's the thing Cas does_ , and Dean smacks his leg with stinging fingertips), looking at Cas with confusion. "Why wouldn't I?"

"I... might be less well-informed of human culture than I thought," Castiel says slowly, "but isn't the sex supposed to come after the dinner?"

Dean looks up at him with all the solemnity he can muster. "And it will."

Sam doesn't make it two seconds before he's sniggering. Cas looks askance at Dean for a moment. Then, the dawning of understanding is a sunrise on his face. "Oh, I see," he says, grinning all gummy and content.

It's almost enough to make Dean say _fuck it_ to apple cobbler for today, and order in.

 _Then again_ , his mind suggests innocently, _you've never fucked Cas in the car, and it's been awhile with Sam... you could have them both in the back seat if you're bendy enough._

"Get your asses in gear," Dean says, smacking a cheek on both. "We're heading out."

"Can we get showers?" Sam asks dubiously. "Cas has got --" (Jizz on his tie. Dean sees it. Dean honestly kind of likes it.

He owes Sam exactly none of that explanation.)

"It's up to you, of course," Dean interrupts, hissing a little when Castiel rises up and he slips out. "Buut you're just gonna get dirty again." He leers up at his brother.

Sam swallows, gaze heating, the corners of his lips twitching up in that incendiary smirk that Dean just loves to see.

They're out the door in ten minutes.

The drive is fairly uneventful, considering the thick-cut sexual tension riding the air in between them. They're all loose-limbed and relatively sated from the sheer ridiculousness of earlier, but they all know it's only a matter of time. Dean puts in BӦC and turns it down to an easy murmur. Sam hums along tunelessly.

Cas is in the back. He always climbs in back there, despite Dean's numerous suggestions that the front will in fact seat three. He's got his elbows up on the seat back between the two headrests, leaning there with his chin on his clasped hands. He's staring straight out at the road.

Dean wonders if he can still feel directions, the pull of the Earth, all that jazz. If he's retained his senses even without all that power behind them, or if he really is just another human now, dim and dulled, with all the limitations of the species.

 _No_ , Dean decides with a sudden vehemence that startles him a little, _Cas will never be 'just another human'. He was the size of the fucking Chrysler building. He had multiple heads and could hop dimensions and sang with the Host of Heaven, and he's_ Cas _. He will never be just your average boring dude._

They pull up to Maylene's as the last reaching tendrils of sunset succumb to the deepening night. The sign is lit, all the letters are working. Inside looks as clean as it ought to. Dean steps out of the car and inhales the cool air feeling like a million bucks.

Two other car doors slam; he looks across the glimmer and black of the roof to see Sam and Cas grinning at him. They both look debauched. Castiel's suit is rumpled, his tie stained beyond repair, and Sam's shirt has a shot collar that pulls to expose a hickey Dean never even noticed Castiel giving. He might feel a little weird about that were it not for their twin expressions, which are explaining at length and in lewd detail exactly what they want to do to him.

Dean pockets the keys.

"Let's get this shit to go."

 

 

 

 

**Author's Note:**

> Thanks for reading! 
> 
> If you liked this fic, please consider leaving kudos/a comment. I really appreciate feedback. ♥


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